A Russian street-kid turned vampire, Dragomir stumbled into the machinations of the Sangiovanni family mostly because he was too clueless to fear them. After that, his unlife became one of strange irony. He tipped the scales of city-wide politics without being interested in them, and had fortune falling in his lap without knowing why. What was ultimately the strangest about Dragomir, however, was how well he always did in spite of being intentionally sabotaged by his player.
Dragomir was the first example of “helping” I've seen, a character whose player almost seemed to have it out for him – he became saddled with phobias, addictions, and obsessions, and yet in spite of his rapidly declining mental health he somehow managed to keep going. He was a great example of a character who creates conflict sometimes merely by existing – the scorpion to Berlin's toad, someone who's destructive not because he wants to, but simply because it is in his nature.
I don't think Dragomir ever reflected on his actions. His player certainly did, and that definitely makes him an iconic character.
The most memorable moments with Dragomir tend to be his failures, for some reason. I think the time he stole a sacrificial dagger out of sheer kleptomania, only to realize he'd just robbed a group of werewolves, may qualify as one of the funniest. Did I mention he had a crippling phobia of dogs?